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Search for 2-Fluoro-L-Phenylalanine丨CAS 19883-78-4
2-Fluoro-L-Phenylalanine is a fluorinated derivative of L-phenylalanine featuring a fluorine atom at the ortho position of the aromatic ring. As a non-proteinogenic amino acid, it provides a useful structural variation for peptide synthesis, medicinal chemistry, and biochemical research. The fluorine substituent can influence electronic properties, molecular interactions, and metabolic behavior, depending on the target structure. Its free amino and carboxyl groups allow it to participate in a range of amino acid coupling and derivatization reactions, making it a valuable building block for specialized research applications.
Chemical Identifiers
| InChI | InChI=1S/C9H10FNO2/c10-7-4-2-1-3-6(7)5-8(11)9(12)13/h1-4,8H,5,11H2,(H,12,13)/t8-/m0/s1 |
| InChI Key | NYCRCTMDYITATC-QMMMGPOBSA-N |
| Smiles | C1=CC=C(C(=C1)C[C@@H](C(=O)O)N)F |
| EC No. | 606-394-6 |
| MDL No. | MFCD00066448 |
| PubChem CID | 716319 |
Applications
Applications in Peptide Synthesis
2-Fluoro-L-Phenylalanine can be incorporated into peptide sequences to introduce an ortho-fluorinated aromatic side chain. Replacing a conventional phenylalanine residue with a fluorinated analogue may influence peptide conformation, local electronic characteristics, and interactions with surrounding molecular groups. This makes the compound useful in the preparation of modified peptides and peptide analogues for studying structure–activity relationships and exploring the effects of amino acid substitution.
Applications in Medicinal Chemistry Research
Fluorinated amino acids are widely used in medicinal chemistry research because fluorine substitution can modify molecular properties without substantially increasing molecular size. 2-Fluoro-L-Phenylalanine can serve as a building block for synthesizing small molecules and peptide-based candidates containing a fluorinated aromatic group. Researchers may use it to investigate how ortho-fluorine substitution affects binding interactions, physicochemical properties, and biological activity within a particular molecular series.
Applications in Protein and Biochemical Research
2-Fluoro-L-Phenylalanine can support research into amino acid analogues, protein structure, and molecular recognition. Fluorinated aromatic residues may provide distinctive spectroscopic or physicochemical characteristics that are useful in selected analytical studies. Depending on the experimental system, this compound may be explored in investigations of protein–ligand interactions, amino acid substitution, and the relationship between molecular structure and biological function.
Applications in Organic Synthesis
The amino and carboxyl functionalities of 2-Fluoro-L-Phenylalanine provide opportunities for esterification, amide formation, protection, and other standard amino acid transformations. Its fluorinated aromatic ring can be retained as a structural feature in subsequent synthetic steps, supporting the preparation of diverse fluorinated intermediates and specialty compounds. It is suitable for research and development projects that require a defined L-amino acid building block with an ortho-fluorinated phenyl group.
